Reagents

• Acetic Anhydride (Ac2O)

  Converts alcohols to acetates (esters). Can be used as a temporary protecting group for alcohols, especially with sugars. Used to convert caboxylic acids to anhydrides. Can also be used in the Friedel-Crafts acylation of aromatic rings.
• Silver Nitrate (AgNO3)

  Will react with alkyl halides to form silver halides and the corresponding carbocation. When a nucleophilic solvent such as water or an alcohol is used, this can result in an SN1 reaction. It can also react in the Tollens reaction to give carboxylic acids from aldehydes. Similar to AgBF4.
• Silver Oxide (Ag2O)

  Used in the Tollens reaction to oxidize aldehydes to carboxylic acids. This is the basis of a test for the presence of aldehydes, since a mirror of Ago will be deposited on the flask. It is also used as the base in the Hoffmanelimination. Similar to AgNO3.
• Aluminum chloride (AlCl3)

  A strong Lewis acid. It can be used tocatalyze the chlorination of aromatic compounds, as well as Friedel-Crafts reactions. It can also be used in the Meerwein-Ponndorf-Verley reduction.Similar to FeCl3, FeBr3, AlBr3.
• Aluminum Bromide (AlBr3)

  Lewis acid, promoter for electrophilic aromatic substitution. Similar to FeCl3, FeBr3, AlCl3.
• Boron Trifluoride (BF3)

  A strong Lewis acid. It is commonly used for the formation of thioacetals from ketones (or aldehydes) with thiols. Similar to FeCl3, AlCl3.
• Borane (BH3)

  Used for the hydroboration of alkenes and alkynes. Similar to B2H6 (“diborane”), BH3•THF, BH3•SMe2, disiamylborane, 9-BBN.
• Bromine (Br2)

  Will react with alkenes, alkynes, aromatics, enols, and enolates, producing brominated compounds. In the presence of light, bromine willalso replace hydrogen atoms in alkanes. Finally, bromine is also used to promote the Hoffmann rearrangement of amides to amines. Similar to NBS, Cl2, I2, NIS, NCS.
• Chlorine (Cl2)

  A very good electrophile. It will react with double and triple bonds, as well as aromatics, enols, and enolates to give chlorinated products. Finally, it assists with the rearrangement of amides to amines (the Hoffmann rearrangement). Similar to NCS, Br2, NBS, I2, NIS.
• Cyanide ion (CN)

  A good nucleophile. It can be used for substitution reactions (SN2), for forming cyanohydrins from aldehydes or ketones, and in the benzoin condensation.Same as KCN, NaCN, LiCN.
• Chromium trioxide (CrO3)

  Oxidant. When pyridine is present, it is a mild oxidant that will oxidize primary alcohols to aldehydes. However, if water and acid are present, the aldehyde will be oxidized further the the carboxylic acid. Similar to PCC (when pyridine is added). When aqueous acid is present, it is the same or similar to Na2CrO4 / K2Cr2O7 /Na2Cr2O7 / H2CrO4 (and KMnO4).
• Copper (I) Bromide (CuBr)

  Reacts with aromatic diazonium salts to give aromatic bromides. Also used to make organocuprates (Gilman reagents).Similar to CuCN, CuCl, CuI.
• Copper (I) Chloride (CuCl)

  Reacts with aromatic diazonium salts to give aryl chlorides; also used to form organocuprates (Gilman reagents) from organolithium salts.Similar to CuCN, CuBr, CuI.
• Copper (I) Iodide (CuI)

  Reacts with alkyllithium reagents to form dialkyl cuprates. Similar to CuCN, CuBr, CuCl.
• DCC (N,N’-dicyclohexanecarbodiimide)

  Primarily used for the synthesis of amides from amines and carboxylic acids. It is, essentially, a dehydration reagent (removes water).
• DMS (Dimethyl Sulfide)

  Used in the “reductive workup” of ozonolysis, to reduce the ozonide that is formed. DMS is oxidized to dimethyl sulfoxide (DMSO) in the process.Similar to Zn (in the reductive workup for ozonolysis).
• Diazomethane (CH2N2)

  Used for three main purposes:

  1) to convert carboxylic acids into methyl esters,

  2) in the Wolff rearrangement, as a means to extend carboxylic acids by one carbon

  3) for cyclopropanation of alkenes.
• Deuterium (D)

  The heavy isotope of hydrogen, having an atomic weight of two. Deuterium has essentially the same reactivity as hydrogen, but due to the different magnetic properties of the nucleus, it can be differentiated from hydrogen in 1H NMR. Deuterium analogs of hydrogen-containing reagents can therefore be useful in introducing deuterium as a "label" for examining stereochemistry and mechanisms.
• DIBAL (Di-isobutyl aluminum hydride)

  Strong, bulky reducing agent. It is most useful for the reduction of esters to aldehydes: unlike LiAlH4 , it will not reduce the aldehyde further unless an extra equivalent is added. It will also reduce other carbonyl compounds such as amides, aldehydes, ketones, and nitriles. Similar to LAH, LiAlH(Ot-Bu)3.
• DMP (Dess Martin Periodinane)

  An oxidizing agent. It will oxidize primary alcohols to aldehydes without going to the carboxylic acid (similar to PCC). It will also oxidize secondary alcohols to ketones. Similar to PCC, CrO3 with pyridine.
• Iron (Fe)

  Will reduce nitro groups to amines in the presence of a strong acid such as HCl. Similar to Sn, Zn.
• Iron (III) Bromide (FeBr3)

  Lewis acid, promoter for electrophilic aromatic substitution. Similar to AlBr3, AlCl3, FeCl3.
• Iron (III) Chloride (FeCl3)

  Lewis acid. It is useful in promoting the chlorination of aromatic compounds with Cl2 as well as in the Friedel-Crafts alkylation and acylation reactions.Similar to AlBr3, AlCl3, FeBr3.
• Grignard Reagents

  Extremely good nucleophile, reacts with electrophiles such as carbonyl compounds (aldehydes, ketones, esters, carbon dioxide, etc.) and epoxides. In addition Grignard reagents are very strong bases and will react with acidic hydrogens.Similar to organolithium reagents.
• Hydrogen (H2)

  Gas is used for the reduction of alkenes, alkynes, and many other species with multiple bonds, in concert with catalysts such as Pd/C and Pt.
• H+ (Anhydrous acid)

  There is actually no such reagent as “H+”, because positive charge never exists without a negative counter-ion. The term H+ is a common shorthand referring to a generic acid wherethe identity of the negatively charged “spectator ion” is not important and no water is present. Similar to H2SO4, TsOH, H3PO4.
• H3O+ (aqueous acid)

  Broadly speaking used for many hydrolysis reactions, as well as when a reaction requires “acid workup”.Same as H2O/H2SO4, H2O/H3PO4.
• Hydrobromic acid (HBr)

  Strong acid. It can add to compounds with multiple bonds such as alkenes and alkynes. It can also react with primary, secondary, and tertiary alcohols to form alkyl bromides. Similar to HCl, HI.
• Hydrochloric acid (HCl)

  Strong acid. As a reagent, it can react with multiple bonds in alkenes and alkynes, forming chlorinated compounds. It can also convert alcohols to alkyl chlorides. Similar to HBr, HI.
• Chromic acid (H2CrO4)

  Strong oxidizing agent. It will oxidize secondary alcohols to ketones and primary alcohols to carboxylic acids.Similar to KMnO4. Same as Jones reagent, K2Cr2O7 / H3O+ , Na2Cr2O7 / H3O+, NaCrO4/ H3O+, KCrO4/H3O+, CrO3/H3O+.
• Mercuric Acetate [Hg(OAc)2]

  A useful reagent for the oxymercuration of alkenes and alkynes. It makes double bonds more reactive towards nucleophilic attack by nucleophiles such as water and alcohols. The mercury is removedby using NaBH4 (or H2SO4 in the case of addition to alkynes).Similar to HgSO4, Hg(OTFA)2.
• Mercuric Sulfate (HgSO4)

  Lewis acid. In the presence of aqueous acid it will perform the oxymercuration of alkynes to ketones. Similar to Hg(OAc)2.
• Hydroiodic acid (HI)

  A strong acid. As a reagent it can add hydrogen and iodine across compounds with multiple bonds. It is also useful for the cleavage of ethers and the conversion of alcohols to alkyl halides. Similar to HBr, HCl.
• Periodic acid (HIO4)

  A strong oxidizing agent. It is most commonly used for the oxidative cleavage of 1,2-diols (vicinal diols) to give aldehydes and ketones. Similar to NaIO4, Pb(OAc)4.
• Nitrous Acid (HNO2)

  Primarily used to convert aromatic amines to diazonium salts, which can be converted into many different compounds via the Sandmeyer reaction. It can also be made from NaNO2 if a strong acid such as H2SO4 or HCl is added.
• Nitric acid (HNO3)

  A strong acid, used as a reagent in the addition of NO2 to aromatic compounds. It will also oxidize primary alcohols and aldehydes to carboxylic acids.
• Hydrogen peroxide (H2O2)

  Used as an oxidant in the hydroboration of alkenes and alkynes, converting the C-B bond into a C-O bond. It is also used in the oxidative workup of ozonolysis, converting aldehydes into carboxylic acids.
• Phosphoric acid (H3PO4)

  A moderately strong acid. The conjugate base of H3PO4 is a poor nucleophile, so phosphoric acid is an excellent acid to use for elimination reactons. Similar to H2SO4, TsOH.
• Sulfuric acid (H2SO4)

  A strong acid (pKa –3.0). It is particularly useful for elimination reactions since its conjugate base [HSO4–] is a very poor nucleophile. It finds use in many other reactions as a general strong acid. Similar to TsOH.
• Iodine (I2)

  An excellent electrophile due to the weak I–I bond (approx 151 kJ/mol [36 kcal/mol]). It reacts with carbon-carbon multiple bonds such as alkenes and alkynes, along with other nucleophiles. It is also used in theiodoform reaction.Similar to NIS.